[(1S,2R,4R,6S,7S,10R,11R,16S,17R,18S)-6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-14-oxo-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadec-12-en-18-yl] acetate

Details

• Internal ID: dcd27226-69af-4897-9dad-ec4699412a7e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4R,6S,7S,10R,11R,16S,17R,18S)-6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-14-oxo-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadec-12-en-18-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C2C(C(=O)C=CC2(C3C1(C45C(O4)CC(C5(CC3)C)C6=COC=C6)C)C)(C)C)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]([C@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1([C@]45[C@H](O4)C[C@H]([C@@]5(CC3)C)C6=COC=C6)C)C)O
• InChI: InChI=1S/C28H36O6/c1-15(29)33-23-21(31)22-24(2,3)19(30)8-10-25(22,4)18-7-11-26(5)17(16-9-12-32-14-16)13-20-28(26,34-20)27(18,23)6/h8-10,12,14,17-18,20-23,31H,7,11,13H2,1-6H3/t17-,18+,20+,21+,22+,23+,25+,26-,27-,28+/m0/s1
• InChI Key: MDSOLYLVXRNZBK-ZJOBNYEKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₆
• Molecular Weight: 468.60 g/mol
• Exact Mass: 468.25118886 g/mol
• Topological Polar Surface Area (TPSA): 89.30 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.42
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9783	97.83%
Caco-2	-	0.6292	62.92%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7637	76.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4270	42.70%
OATP1B3 inhibitior	-	0.6103	61.03%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7043	70.43%
P-glycoprotein inhibitior	+	0.6609	66.09%
P-glycoprotein substrate	-	0.5619	56.19%
CYP3A4 substrate	+	0.7083	70.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8691	86.91%
CYP3A4 inhibition	+	0.7490	74.90%
CYP2C9 inhibition	-	0.8394	83.94%
CYP2C19 inhibition	-	0.8573	85.73%
CYP2D6 inhibition	-	0.9366	93.66%
CYP1A2 inhibition	-	0.8375	83.75%
CYP2C8 inhibition	+	0.5297	52.97%
CYP inhibitory promiscuity	-	0.9160	91.60%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4870	48.70%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9387	93.87%
Skin irritation	-	0.6564	65.64%
Skin corrosion	-	0.8962	89.62%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7092	70.92%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5551	55.51%
skin sensitisation	-	0.8395	83.95%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5758	57.58%
Acute Oral Toxicity (c)	I	0.4409	44.09%
Estrogen receptor binding	+	0.8268	82.68%
Androgen receptor binding	+	0.7416	74.16%
Thyroid receptor binding	+	0.6604	66.04%
Glucocorticoid receptor binding	+	0.8212	82.12%
Aromatase binding	+	0.7011	70.11%
PPAR gamma	+	0.6759	67.59%
Honey bee toxicity	-	0.7582	75.82%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9949	99.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.99%	94.45%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	92.96%	81.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.96%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.70%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.29%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.87%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.84%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.01%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.78%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.77%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.33%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.16%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.33%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.56%	98.95%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.86%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.35%	89.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	83.69%	87.67%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.21%	94.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.02%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.94%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.74%	94.08%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.33%	93.00%

Plants that contains it

• Azadirachta indica

Cross-Links

• PubChem: 162897369
• LOTUS: LTS0069992
• wikiData: Q105161937